Patent GB-364092-A (GB)
Title: Improved manufacture of oxidizable organic compounds, particularly rubber, oils, soaps and aldehydes
IPC: C11B5/00
Filed: 1930-09-23
Abstract: Antioxidants for oils and soaps have the general formula R-CH2-R1-NH2, where R is anilino, amino substituted anilino, alkyl substituted anilino, amino alkyl substituted anilino, alkyl amino substituted benzene, or amino substituted benzene, and R1 is alkyl substituted benzene, amino substituted benzene or alkyl amino substituted benzene. Particular preferred forms are H2N-R-CH2-R1-NH2, where R or R1 or both are alkyl substituted benzene, amino substituted benzene or alkyl amino substituted benzene and R-NH-CH2-R1 where R is a member of the benzene series and R1 is an amino substituted member of the benzene series.  The following substances are given as examples:--p amino benzyl aniline, p-amino-m-xylyl-p-toluidine, 4 : 41-diamino-di-o-tolyl-methane, 2-4-41-triamino-5-methyl-diphenyl-methane, 4-41-diamino-3-methyl - diphenylmethane, and 6 - 4-41 - triamino-3 - 31 - dimethyl - diphenylmethane.  The general method of preparation is illustrated by the preparation of p-amino-benzyl-aniline, which is prepared by reacting 55 parts of aniline with 7,5 parts of formaldehyde, the oily material thus formed (N-N1-diphenyl-methylene-diamine) being then reacted with 27,5 parts of aniline hydrochloride, the product being treated with dilute sodium hydroxide, and steam distilled to remove the aniline.ALSO:Anti-oxidants for rubber, oils, soaps, aldehydes (e.g crotonaldehyde), and other oxidizable organic compounds have the general formula R-CH2-R1-NH2, where R is anilino, amino-, substituted anilino, alkyl-substituted anilino, aminoalkyl-substituted anilino, alkylamino-substituted benzene, or amino-substituted benzene, and R1 is alkyl-substituted benzene, amino-substituted benzene or alkylamino-substituted benzene, and are prepared by treating the reaction product of arylamines and aldehydes with amine hydrochlorides.  The following substances are specified: -- p - aminobenzylaniline, p-amino-m-xylyl-p-toluidine, 4 : 4<1> - diamino - di-o-tolylmethane, 2 : 4 : 4<1> - triamino - 5 - methyl - di - phenylmethane, 4 : 4<1>-diamino-3-methyldiphenylmethane, and 6 : 4 : 4<1>-triamino-3 : 3<1>-dimethyldiphenylmethane.  The general method of preparation is illustrated by the preparation of p-aminobenzylaniline, which is prepared by reacting on aniline with formaldehyde, the oily material thus formed (N-N<1> diphenylmethylenediamine) being then treated with aniline hydrochloride.  Diagrammatic illustrations of and references to the preparation of 4-4<1>-diamino-di-o-tolyl-methane, and 4-4<1>-diamino-3<1>-methyldiphenylmethane are also given.ALSO:Antioxidants for rubber, oils, soaps, and aldehydes have the general formula R-CH2-R1-NH2, where R is anilino, amino substituted anilino, alkyl substituted anilino, amino alkyl substituted anilino, alkyl amino substituted benzene, or amino substituted benzene, and R1 is alkyl substituted benzene, amino substituted benzene or alkyl amino substituted benzene.  Particular preferred forms are H2N-R-CH2-R1-NH2, where R or R1 or both are alkyl substituted benzene, amino substituted benzene or alkyl amino substituted benzene and R-NH-CH2-R1 where p  R is a member of the benzene series and R1 is an amino substituted member of the benzene series.  The following substances are given as examples:-p-amino benzyl aniline, p-amino-m-xylyl-p-toluidine, 4.41-diamino-di-o-tolyl-methane, 2-4-41-triamino-5-methyl-diphenyl-methane, 4-41-diamino-3-methyl-diphenylmethane, 6-4-41 - triamino-3 - 31 - dimethyl - diphenylmethane.  References are given to literature for all these compounds.  Tables are furnished showing the efficacy of the products in rubber mixes.